5,6-Dihydroxytryptamine

5,6-Dihydroxytryptamine

Clinical data
Other names	5,6-DHT
Identifiers
IUPAC name 3-(2-aminoethyl)-1H-indole-5,6-diol
CAS Number	5090-36-8
PubChem CID	21163
ChemSpider	19902
UNII	W2QY253O8S
ChEMBL	ChEMBL303916
CompTox Dashboard (EPA)	DTXSID40198930
ECHA InfoCard	100.023.464
Chemical and physical data
Formula	C10H12N2O2
Molar mass	192.218 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1=C2C(=CC(=C1O)O)NC=C2CCN
InChI InChI=1S/C10H12N2O2/c11-2-1-6-5-12-8-4-10(14)9(13)3-7(6)8/h3-5,12-14H,1-2,11H2 Key:SKOKLDQYOKPCPU-UHFFFAOYSA-N

5,6-Dihydroxytryptamine (5,6-DHT) is a monoaminergic neurotoxin and tryptamine derivative related to serotonin (5-hydroxytryptamine) and 5,7-dihydroxytryptamine (5,7-DHT). ^{[1] [2] [3]} It is a relatively selective serotonergic neurotoxin, but also acts as a dopaminergic and noradrenergic neurotoxin at higher doses. ^{[1] [2] [3]} In addition, it produces widespread generalized toxicity at higher doses. ^[1] Its selective serotonergic neurotoxicity is due to its high affinity for the serotonin transporter (SERT). ^[2] Because of its SERT affinity, 5,6-DHT has activity as a serotonin reuptake inhibitor. ^[1]

The compound can be used in scientific research to lesion the brain serotonergic system in animals. ^{[1] [2] [3]} It has a number of limitations and disadvantages relative to 5,7-DHT however, which have made 5,7-DHT a more preferred serotonergic neurotoxin in scientific research. ^{[3] [1] [2]} Administration of 5,6-DHT (and 5,7-DHT) to animals causes dramatic behavioral changes. ^[1]

5,6-DHT was first described in the scientific literature by 1971. ^{[1] [2] [3] [4]}

See also

• 4,5-Dihydroxytryptamine
• 6,7-Dihydroxytryptamine
• 4-Hydroxy-5-methoxytryptamine

References

1. Paterak J, Stefański R (2022). "5,6- and 5,7-Dihydroxytryptamines as Serotoninergic Neurotoxins". Handbook of Neurotoxicity. Cham: Springer International Publishing. pp. 691–717. doi:10.1007/978-3-031-15080-7_76. ISBN   978-3-031-15079-1.
2. Kostrzewa RM (2022). "Survey of Selective Monoaminergic Neurotoxins Targeting Dopaminergic, Noradrenergic, and Serotoninergic Neurons". Handbook of Neurotoxicity. Cham: Springer International Publishing. pp. 159–198. doi:10.1007/978-3-031-15080-7_53. ISBN   978-3-031-15079-1.
3. Baumgarten HG, Lachenmayer L (2004). "Serotonin neurotoxins--past and present". Neurotoxicity Research. 6 (7–8): 589–614. doi:10.1007/BF03033455. PMID   15639791.
4. Baumgarten HG, Björklund A, Lachenmayer L, Nobin A, Stenevi U (1971). "Long-lasting selective depletion of brain serotonin by 5,6-dihydroxytryptamine". Acta Physiologica Scandinavica. Supplementum. 373: 1–15. PMID   5291907.